The constituents of the rhizome and roots of Caulophyllum thalictroides / by Frederick B. Power and Arthur H. Salway.

  • Power, Frederick B. (Frederick Belding), 1853-1927.
Date:
1913
Catalogue details

Licence: In copyright

Credit: The constituents of the rhizome and roots of Caulophyllum thalictroides / by Frederick B. Power and Arthur H. Salway. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    [a]D — 221‘6°), which haa been identified as methylcytisine; the pier ate melts at 228°. (ii) A crystalline glucoside, caulosaponin, C54H880]7,4H20 (m. p. 250—255°), which yields a deca-actlyl derivative, C54H78O17(CO*CH3)j0, melting at 135—140°, and on hydrolysis is resolved into caulosapoyenin, C42H6fi°0 (ra- P- 315°), and dextrose. Caulosapogenin yields a tetra-acetyl derivative, C42H6206(C0• CH3)4, melting at 120°, and a diacetyl derivative, C42HC4Oc(CO,CH3)2, melting at 160—162°, from which a crystalline monosodio-derivative, C42H63OcNa(CO,CII3)2, was prepared; it yielded, furthermore, a tetrab enzoyl derivative, c42hC2o0(co-c6h3)4, melting at 288°, and a monomethyl ether, C42Hg5°5(°'CH3), which melts at 235°. (iii) A new crystalline glucoside, caulophyllo- saponin, C6CH104O17 (m. p. 250—260°; [a]D +32’3°), which yields a deca-acetyl derivative, Ce6H94O17(CO'CH3),0, melting at 155—160°, and on hydrolysis is resolved into caulophyllosapogenin, C56H8809 (m. p. 315°), and arabinose. Caulophyllosapogenin yields a hexa-acetyl derivative, C56H8209(C0-CH3)6, melting at 160—162°, and a dimethyl ether, C50H86O7(O-CH3)2, which melts at 240—242°, and has [a]D +43‘6°. (iv) A phytosterol, C27H4G0 (m. p. 153°). (v) Citrullol, C28H4502(0H)3. (vi) A mixture of fatty acids, con- sisting of palmitic, stearic, cerotic, oleic and linolic acids. The alcoholic extract also contained a quantity of sugar, which yielded c^-phenylglucosazone (m. p. 210°), and a comparatively small amount of resinous material. The above-mentioned methylcytisine, C12H16ON2, represents the alkaloid previously obtained by J. U. Lloyd (Proc. Amer. Pharm. Assoc., 1893, 41, 115), and designated “ caulophylline,” but he did not succeed in crystallising the base, and its composition was not determined. In view of its present identification, the name “caulo- phylline ” should no longer be retained for this alkaloid. The compound designated by the present authors as caulosaponin, C34H88017,4Ho0, is undoubtedly identical with a crystalline gluco- side first obtained by J. U. Lloyd (“Drugs and Medicines of North America,” Vol. II, 1887, p. 151), and termed by him “leontin,” although the formula deduced from its analysis was not correct. As it has now been completely characterised, it appears desirable that it should receive the new and distinctive name assigned to it. For the purpose of determining the physiological action of methylcytisine and the two above-mentioned crystalline glucosides, caulosaponin and caulophyllosaponin, some tests were kindly con- ducted for us by Dr. P. P. Laidlaw, of the Wellcome Physiological Research Laboratories, to whom our best thanks may here be expressed. Methylcytisine has been found to be very similar in its action to